0001140361-25-043369 Sample Contracts

FIRST SUPPLEMENTAL INDENTURE between Bowhead Specialty Holdings Inc., and Dated as of November 25, 2025 (Supplement to the Indenture, dated as of November 25, 2025)
First Supplemental Indenture • November 25th, 2025 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • New York

This First Supplemental Indenture, dated as of November 25, 2025 (this “Supplemental Indenture”), is entered into by and between Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”) and U.S. Bank Trust Company, National Association, as trustee (the “Trustee”).

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Bowhead Specialty Holdings Inc. Underwriting Agreement
Underwriting Agreement • November 25th, 2025 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • New York

Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), proposes to issue and sell to the several Underwriters listed in Schedule 1 hereto (the “Underwriters”), for whom you are acting as representatives (the “Representatives”), aggregate $150,000,000 principal amount of its 7.750% Senior Notes due 2030 (the “Securities”). The Securities will be issued pursuant to an Indenture to be dated as of November 25, 2025 (the “Base Indenture”) between the Company, and U.S. Bank Trust Company, National Association, as trustee (the “Trustee”), as amended and supplemented including by the Supplemental Indenture, to be dated as of November 25, 2025 (together with the Base Indenture, the “Indenture”) between the Company and the Trustee.

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